Y. Kubo, T. Inoue, H. Sakai
Sep 1, 1992
Citations
0
Influential Citations
19
Citations
Journal
Journal of the American Chemical Society
Abstract
Irradiation of dimethyl 1,4-naphthalenedicarboxylate (1) with various alkenes 2, and 10a-d is found to give novel 1,8-adducts 3, 11a-d, 12a,b,d, and 13b,d. The 1,8-photoaddition proceeds with retention of the stereochemistry of the alkenes in the reactions with trans- and cis-2-butene (5 and 7). Because there is no evidence for a preformed ground-sate complex between 1 and the alkalenes, the 1,8-addition proceeds from the singlet excited state of 1